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Volumn 25, Issue 10, 2007, Pages 1409-1412

A facile synthesis of indole-based conjugated derivatives

Author keywords

Indole; Intermediate; Synthesis

Indexed keywords

EID: 36549062430 PISSN: 1001604X EISSN: None Source Type: Journal
DOI: 10.1002/cjoc.200790260 Document Type: Article

Times cited : (6)

References (25)

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- Synthetic procedure and characterization data of 6: a mixture of N-(2-hydroxyethyl)indole (12.9 g, 80 mmol, paraformaldehyde (2.55 g, 80 mmol, triphenylphosphine (21.0 g, 80 mmol, potassium iodide (13.3 g, 80 mmol, and acetic acid (16.0 g) in chloroform was stirred for 10 min. Then few drops of water were added, and the resultant clear reaction mixture was agitated at room temperature for three weeks. After separated by decantation, the organic phase was dried over Na2SO4, and evaporated to give a solid which was collected by filtration and washed several times with water and diethyl ether. Recrystallization from ethanol gave a white solid (23.0 g, 51.1, 1H NMR (300 MHz, CDCl3) δ: 7.70 -7.65 (m, 3H, ArH, 7.54-7. 40 (m, 12H, ArH, 7.28-7.25 (m, 1H, ArH, 7.08 (d, J=3.6 Hz, 1H, ArH, 7.05-7.00 (m, 1H, ArH, 6.84-6.73 (m, 2H, ArH, 4.46 (d, J=12.6 Hz, 2H, CH2PPh3I, 4.09 t, J
- 3) δ: 135.3, 134.5, 134.4, 132.2, 130.5, 130.4, 129.3, 124.8, 121.0, 118.3, 117.8, 113.0, 111.5, 97.6, 46.5, 32.2, 20.0, 13.8.

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25
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- Synthetic procedure and characterization data of 8: 6 (0.62 g, 1.20 mmol) was suspended in 10 mL of anhydrous tetrahydrofuran under nitrogen. t-BuOK (0.27 g, 2.40 mmol) was added directly as a solid, and the resultant mixture was stirred at room temperature for 10 min. After the addition of the solution of p-nitrobenzaldehyde (0.15 g, 1.00 mmol) in anhydrous tetrahydrofuran (10 mL) dropwise, the reaction mixture was stirred at room temperature overnight, then poured into 100 mL of water. The organic product was extracted with chloroform, and dried over anhydrous Na2SO 4. After removing the solvent, the crude product was purified through a silica gel column chromatography by using chloroform/ethyl acetate (V, V=6:1) as eluent, to give the products 8 of cis (0.09 g, 24.5, and trans isomers (0.22 g, 59.7, m.p. of the trans product: 137-140°C; UV-Vis of the trans product THF, 2.2 × 10-5
- -1.

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